#25: Dating While Building a Startup

One aspect of startup life that no one seems to talk about is dating. I only have one rule for dating and its to never date someone who works at my company. Nothing good can come of it. Did that at one of my first internships in college and it backfired like one of the Coyote’s traps for the Roadrunner. She was a nightmare to get rid of and I never worked for a tech company in New York City again because of it.

I realized last week that I had to start making an effort to get out of the office and meet other people not in the tech community. People in tech here in Kitchener-Waterloo hangout out with other tech people, almost exclusively. It’s actually pretty sad. For all the great things about this community it is often hard to convince your bottom of the rung software engineer to get out of the office and grab a drink with people they don’t work with. Hence, why I’m pushing myself to meet non-tech people when dating.

I’ve joined a couple dating sites and of course Tinder, but I think Tinder is lost on me. As much as I enjoy the idea of dismissing something with a simple swipe of my thumb, I don’t think that’s conducive to finding a significant other. Even those terrible dating videos from the 80’s were at least 60 seconds long, forcing you to listen to the person talk for an excruciatingly long time.

The dating scene is rough. Jasper did the right thing. He met someone who made him better and went for it before starting his own business. Starting a business I’ve been told is like raising a child. I get the analogy, but I think it only applies it you’re the only one in the business. I think starting a business is like a building a romantic relationship.

With a child, you love them unconditionally. With a relationship you can love and hate the person at the same time. Building a business with a team of great people is exactly like. So trying to build a business and build a lasting relationship at the same time is a complete bitch.

For example, last week I went out for drinks with a very lovely young woman, a professional in the area, and midway through I received a call with an emergency from Alison. I had to excuse myself for a couple minutes and take the call to put out the fire that popped up. The date did not take it well.

She flipped out. I mean, she threw a drink at me freaked out.

I came back to the table and said, “Sorry about that. A problem at the office.”

“Whose Alison?” my date asked as she crossed her arms.

“She’s my one of my company’s co-founders,” I replied taking a drink of my beer.

“Sure she is,” the girl said standing up in a huff. “You and Alison can now go out on your date. Sorry I was in your way asshole.” And then a vodka-Sprite was splashed in my eyes. What the movies don’t tell you is that vodka in your eyes stings like a motherfucker. At least the drink was clear.

Building a startup can create jealousy, anger, distraction, distance issues during business trips, and often it creates compatibility issues. If there other person doesn’t know what it’s like to be an entrepreneur or work for a tech startup they can’t understand when you have to pull 14-hour days. You then end up dating other startup founders or entrepreneurs and then you have the problem of never seeing them.

It’s a cycle of hell that never seems to end. I should have just married my college girlfriend.